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Why I Choose to Pursue the Pervier Side of Life

I have a weird relationship with my tailor. He’s a smiley, petite, ancient Japanese man who speaks roughly seven words of English, but unexpectedly, over the past few years, we’ve grown pretty close. Maybe even too close? He fingered me, basically. Well . . . ish. It’s complicated.

I’m an obsessive online shopper of vintage clothing. I also have hips that are 12 inches wider than my waist, which means I frequently need my clothes altered. A few years ago, after moving from Brooklyn to Manhattan, I was in search of a new tailor. Yelp bought the two of us together, but it was his warm, wrinkled smile and his masterful ability to restructure a shoulder that convinced me he was the one. We couldn’t communicate verbally but made it work through an embarrassing game of alterations-based charades.

Our relationship was purely professional—he helped me in my quest to dress like a slutty senator’s wife, and I (over)paid him for it—until the fateful day when it veered into a strange gray area.

That morning, I rushed out of the house, and it wasn’t until I was behind the tailor’s curtain that I realized I’d forgotten to wear underwear—a slightly awkward situation when you’re having a miniskirt altered into a micro-skirt. I told myself he wouldn’t notice, which was dubious, given that the process of hemming a skirt always involves him kneeling in front of me with his face at precisely vagina level. Still, I went with it. But then, mid-hem, I felt him graze my bare butt with his hand—just lightly enough that it could have maybe been an accident. Both of us acted oblivious and just moved along like nothing happened. When I left, he hugged me—a hug that, unless I’m insane, conveyed a hint of gratitude for the peep show.

The next time I visited the tailor, a month or so later, I forgot my underpants again—but this time it was on purpose. Sort of creepy, but I guess that’s just my personality? Mainly, it was an investigative tool: I wanted to know if the butt graze was truly a slip of the hand or if he had taken my commando state as a sign of . . . something. (I’m a serious journalist.) That day, while on his knees, the tailor touched my butt again—but this time it was a firm squeeze. I replied with a quiet laugh, and he looked up and gave me a modest head nod. It was the subtlest exchange, but the message was resoundingly clear: Going forward, we are both down to be low-key weird with each other, while continuing to pretend that everything’s totally normal. And with that, we’d entered a pact.

Over the following two years, our unspoken grope exchange intensified ever so slightly with each visit. A butt grab escalated to a boob graze, which escalated to a light peck of the lips on the back of my thigh. Each time he touched me I responded the same way I had from the start—with a giggle, basically. For some reason, I liked seeing how far he would take it. I found it bizarrely hot to stand at attention as he made tiny adjustments to my clothes, waiting for him to pounce.

Until the day he swiped my vagina. I say swiped because I can only describe it as the motion one makes when scrolling through Instagram—slowly, from the back to the front of my pussy. So not technically fingering, but there was definitely fluid exchange. It felt like consummation, somehow. When the alterations and fondling were complete, we hugged it out—an embrace of mutual gratitude—but afterward I knew I could never go back. Once your tailor swipes your vagina, there’s just nowhere to go from there. (And if you’re wondering, yes, I wrote him a gushing Yelp review. And no, he never gave me a discount. I’m not that kind of girl. I only take cash.)

There’s something about these awkward, ambiguous sexual situations that I love— they’re gross in a hot way (which I guess is basically the definition of perversion?). And given how often I’ve found myself in similar exchanges over the years, I think I must attract them. Or at least, I have some skill in the bodily art of saying yes without actually saying “yes.” It’s like flirting: Someone lights a flame and you can either dismiss it or escalate it. You can either smile uncomfortably and pretend to need the bathroom, or you can lean in so far that your nipple slips out and you pretend not to notice. I’m pretty sure this is what everyone’s talking about when they say the “language of love.”

Sometimes these interactions are even less explicit than my tailor situation. For instance, my ambiguously perverted relationship with my orthodontist. Now, obviously, I understand that my orthodontist is professionally required to put his hands in my mouth, but there’s just something about the way he does it—there’s an energy there. Like when he was taking impressions for my Invisalign (the foundation of modern romance), and I could tell he kept his fingers in there just a little too long. And so I accidentally-on-purpose tongued his fingers, and I could tell he liked it. (At least, I hope?)

In our post-woke era of sexual anxiety, we all know that gray areas can be dangerous—they rely on a tenuous mutual understanding that could be broken by misunderstanding at any point—but that’s precisely what makes them so exciting. Clearly, in some situations, verbal consent is necessary, and that too can be superhot. When executed correctly, simply being asked “Can I fuck you?” has been enough to make me wet. But in other cases, laying it all on the table truly kills the vibe. So if my orthodontist had asked me, “Can I leave my fingers lingering in your mouth for just a little bit too long?” I’d be like, “Eww, no. And you should be in jail.” But do it without asking and I’ll tongue your latex gloves all morning.

Recently, at dinner, I asked two of my female friends: Have you ever found yourself wandering the pervy gray area between mundane life and sex? Both, of course, had a story—hence why I hang out with them.

“I work from home and spend a lot of time wandering around the house naked,” said Kara, a 30-year-old photographer. “About a year ago I moved into a building with floor-to-ceiling windows, and I never bothered to get curtains, because I sort of liked the idea that someone could be watching, but I never spotted anyone—until recently.”

According to Kara, there’s a guy across the street who lately has been doing a lot more laptop-ing from his living room, in direct view of her one-woman nudist colony: “I’ve never seen him blatantly staring at me, but I can tell he’s aware. So now when he’s there, I’m always picking things up off the floor or stretching, as an allusive way of saying ‘I know you’re looking.’ It gives me this little sexual charge. Honestly, I don’t even use porn as much anymore since I discovered answering emails with my tits out.” She sighed. “Annoyingly, my boyfriend’s nagging me to get curtains, because he’s freaked out about privacy. I don’t get it—I just assumed everyone thinks being watched naked is hot?”

Lisa, a 28-year-old book editor, butted in. “I think my story counts?” she said nervously. “Last year, I went to a 24-hour screening at an art gallery in Soho and sat next to this man for seven hours in the dark, and slowly over time we inched our hands closer and closer together. We never looked at each other, but eventually our knees were lightly touching, and our hands, which were clammy with nerves, were overlapping on the seat between us.” She paused, flushed. “I think it’s the most erotic thing that’s ever happened to me. But then I ran out. It was just too intense to handle.”

Or perhaps she just reached her climax. In situations like these, you’re not looking to actually fuck, but there is a natural end point, and that is part of what’s great about them. There’s no expectation that it will become something “real” (like, I’m not going to bring my geriatric tailor home to meet my parents). It’s more about finding the erotic in the painfully normal. There’s something thrilling about the Russian roulette of it all. If you read each other right, you get to enjoy this bizarre, dangerous, incredibly intimate dance of pervy mutuality. And then you get to bail.